反应详情

温度

23 °C

To a stirred solution of commercially available 2-amino-6-chlorobenzyl alcohol (CAS-no. 39885-08-0) (315 mg, 2 mmol) in tetrahydrofuran (4 ml) at 23° C. was added commercially available (R)-(−)-1-indanyl isothiocyanate (CAS-no. 737000-97-4) (324 ul, 2 mmol) and the mixture was stirred at 23° C. for 18 h, then at reflux for another 3 h. Cooled to 23° C., the solvent was removed in vacuum, the residue was dissolved in acetonitrile (4 ml), added dicyclohexylcarbodiimide (DCC) (619 mg, 3.0 mmol) and refluxed for 2 h. Cooled to room temperature, diluted with ethyl acetate and water, added little 1 M NaH2PO4.2H2O solution to achieve pH 4, separated phases, washed organic layer with brine and dried over sodium sulfate. Removal of the solvent in vacuum left a yellow foam, which was purified by silica gel flash chromatography with n-heptane and ethyl acetate to give the title compound as a light yellow oil (215 mg, 36%), MS (ISP) m/e=299.1 [(M+H)+].

1. temperatureat reflux for another 3 h
2. temperatureCooled to 23° C.
3. customthe solvent was removed in vacuum
4. dissolutionthe residue was dissolved in acetonitrile (4 ml)
5. temperaturerefluxed for 2 h
6. temperatureCooled to room temperature
7. customseparated phases
8. washwashed organic layer with brine
9. dry with materialdried over sodium sulfate
10. customRemoval of the solvent in vacuum
11. waitleft a yellow foam, which
12. customwas purified by silica gel flash chromatography with n-heptane and ethyl acetate